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Patented Nov. 6, 1951 nrriinfts oF'PonYcHLofio' METHANE' A liavigl M.Musser, Fair LawnyNs 1.", assignor. to.

Pacific Mills, Boston,

Massachusetts Mass.,; a. corporation of l I o. -.-l )rawing. Originalapplication l iug usif 3i; 1946, Serial N0. 694,422. Divided all! thisplication December 23, 1950;8eriaiNo: 202,570

processes" ior preparing this;v composition. The

present application is a' division of my prior ap' u aucnser n No.694,422, filed August 31, 1 946, new Ratent' No. 2,559,986, datedJuly10,1951.

Pathogenic germs are frequently present or on the surface oftextilefabrics, either as a e ul 9 cont t. o the fa i w t e human body,as in the case of sheets, pillowcases, towels and the like, or as aresult of exposure of the textile to an atmosphere in which suchbacteria are present. These germs cling tenaciously to the textilefibers and may, under favorable moisture and temperature conditions,spread and grow colonies, which then present a serious danger ofcontamination. Means have long been sought for rendering a textilematerial permanently antagonistic or resistant tosuch bacteria so as toprevent their growth into colonies and to lessen the danger oicontamination from contact with the textile material. It has beenproposed to overcome this contamination hazard by applying to textilefabric a coating oi' fa, germicidal compound such as mercurial, aphenolic, or like compound. Such compounds are adequately bacteriostaticin this relationship, but the art heretofore has not succeeded inrendering textile materials permanently bacteriostatic by treatment withthem. Fabrics coated with suchmaterials commonly lose substantially allof their bacteriostatic property upon a single laundering and it istherefore necessary that the coating treatment be repeated each time thearticle is laundered Such coating processes require considerablemechanical equipment and, therefore, are -notja practicable procedurefor use in most hotels, hospitals and private homes in which bed linensand towels are used.

It is an object of the present invention to provide improvedbacteriostatic compounds and processes for making the same, suitable foruse in finishing cellulosic materials such as textile fabrics, threads,yarns and fibers, toimpart thereto improved bacteriostatic propertieswhich will be retained more or less indefinitely.

The novel bacteriostatic and hydrophilic compounds of the presentinvention comprise derivatives of 2,2'-dihydroxy3,5,6,3',5',6'-hexach1orodiphenylmethane having the general formula OHOR C! -CH2 C1 Cl Cl wherein R represents one of the group of radicalscomprising CH2--CHOH-CHz-O--CH2CI, and

I ris-verdant that the desirable property of iii-E hibiting' the growthoi bacteria' may be ed to 'c iiIOSi ma-terial by treatment of the are:rial, involving chemical reaction, in which my novel bacteriostatic andhydrophilic compound is attached to the cellulose'molecul'eat the hydro=carbon c ain, represe ted by R in the above rerinula. The combinationofbactericidal and by drophilic groupsemployed in the present inven timincreases the afiinity of the cellulose for water but'without, however,causing it to reach a degree of solubility undesirable in textile materials. The resulting modified cellulosic materials provide abacteriostatic environment which restricts the growth of bacteriathereon under all conditions of moisture and temperature.

The bacteriostatic and hydrophilic compounds of the present inventionare formed by reacting one of the hydroxyl groups of the chlorinatedhydroxy diphenyl methane represented by the for-'- inula withchlorinated 'elycerine, paraforihaldehyde and hydrochloric acid toprovide thereon a Hy: droxyl'ate'd hydrocarbon chain. the finishedcellulose product this hydrocarbon chain is an tached to the cellulosemolecule. H

' The following e ainm'e, given by way of illustration and not o'flimitation of the invention, shows a practical method for thepreparation of bacteriostatic and hydrophilic compounds suitable for usein finishing cellulosic textile material, and practical methods forfinishing such material to provide cellulosic materials having improvedbacteriostatic properties.

Example 2,2-dihydroxy 3,5,6,3',5,6'-hexachlorodlphenylmethane isdissolved in ethyl alcohol and metallic sodium is added slowly to thissolution in molar equivalents (1 mol of Na to 1 mol of diphenylmethane)to form a sodium phenolate. The solution is heated to the boiling pointand a-monochloroglycerine is added slowly in molar proportions, i. e., 1mol of glycerine to 1 mol of diphenylmethane, with the formation of asodium chloride precipitate. The alcoholic solution is recovered byfiltration, and the alcohol evaporated or distilled 01?, leaving aresidue having a melting point of 97 C. This residue is dissolved inbenzene and then paraformaldehyde is added to the solution in molarproportions (1 to 2 mols of paraformaldehyde' tol mol of the compound).Gaseous hydrochloric acid is passed through the benzene solution untilthe paraformaldehyde is.

completely dissolved. The solution is then neutralized with pyridine,using litmus paper as an indicator.

The compound contained in the resulting solution may be applied totextile'fabrics in anyone of the three following ways, to form acellulose derivative which is bacteriostatic (A) Cotton fabric ispretreated with a 'to solution of sodium acetate, and squeezed to about100% pickup. The treated fabric is then impregnated with a 1% to 2%solution of the compound in benzene. I The cloth is passed throughsqueeze rolls (about 80% to 100% pickup) and then heated to about130-150" C.

(B) The neutralized benzene solution is evaporated on a water bath andthe solid residue dispersed in warm water by stirring. The textilefabric to be treated is pretreated with sodium acetate as in (A) above,and then impregnated with the water dispersion. Thereafter the fabric isheatedto 130150 C.

(C) The neutralized benzene solution is evapo- 4 rated and the solidresidue dispersed in a warm water solution of 5% to 10% sodium acetate.The textile fabric is impregnated directly, without pretreatment, withthe water dispersion, and the losic nature, either native orregenerated, on

which there are free hydroxyl groups. Cellulosic textile materials, suchas cotton and other natural products, may be treated in the form offibers, threads, yarns, or in the piece, as a woven, braided, netted orknitted fabric. Such treatment involves a chemical reaction upon thecellulose molecule with the production of a new cellulosic substance.The bacteriostatic qualities of this substance are not impaired bywashing, dyeing or other treatments usually encountered in the finishingor use of textile material.

The foregoing disclosure of preferred embodiments of my invention ismade by way of illustration and not of limitation. It will beappreciated that changes may be made therein by those skilled in the artwithout departure from my invention, as expressed in the followingclaims.

I claim: 1. Hydrophilic and bacteriostatic compounds 7 of the grouphaving the general formula OH on I g 7 01 on 01 wherein R represents oneof the group of radicals consisting of -CH2CHOHCH2O-CH2C1,

and" b cm-o-omm cH-o O-CHzCl 2. The method for the preparation of aderivative of chlorinated diphenyl methane which comprises reactingmonochlorglycerine with 2,2- dihydroxy 3,5,6,3,5,6-hexachlorodiphenylmethane in the presence of metallic sodium andthereafter reacting with paraformaldehyde and gaseous hydrochloric acid.I

3. The hydrophilic and bacteriostatic compound represented by theformula OCH1-CHOH-CHrOOHzCl 4. The hydrophilic and bacteriostaticcompound represented by the formula DAVID M. MU SSER,

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Musser July 10, 1951

1. A HYDROPHILIC AND BACTERIOSTATIC COMPOUNDS OF THE GROUP HAVING THE GENERAL FORMULA
 2. THE METHOD FOR THE PREPARATION OF A DERIVATIVE OF CHLORINATED DIPHENYL METHANE WHICH COMPRISES REACTING MONOCHLORGLYCERINE WITH 2,2''DIHYDROXY 3,5,6,3'',5'',6''-HEXACHLORODIPHENYLMETHANE IN THE PRESENCE OF METALLIC SODIUM AND THEREAFTER REACTING WITH PARAFORMALDEHYDE AND GASEOUS HYDROCHLORIC ACID. 